Anionic Organotin Compounds in Organic Synthesis - Trialkylstannyllithium And Trialkylstannylmethyllium -

Synthetic use of the title compounds is reviewed, placing emphasis on the multiple functioning properties based on the organotin chemistry. 1. Introduction 2. General Scope of Organotin Chemistry 3. Classification of Tin Reagents 4. Trialkylstannyllithium 4.1.Reaction with Carbonyl Compounds 4.2.Reaction with α,β- Unsaturated Aldehydes 4.3.Reaction with α,β-Unsaturated Ketones 4.3.1. Activation by γ-Hydroxyl Leaving Group 4.3.2. Activation by Radical Participation 4.3.3. Activation by γ-Keto Group 4.3.4. Oxidative Activation 4.4.Reaction with α,β-Unsaturated Sulfones 4.5.Reaction with Substrates Containing Leaving Groups 4.5.1. Aromatic or Vinylic Activation 4.5.2. 1,2-Type Activation 4.5.3, 1,3-Type Activation 4.5.4 Activation by Cationic Center Separated by More Than Three Carbons 5. Trialkylstannylmethyllithium 5.1.Reaction with Carbonyl Compounds 5.2.Reaction with Oxiranes 5.3.Reaction with α-Chloro Ketones 5.4.Reaction with α,β-Epoxy Ketones 5.5.Reaction with Esters 6. Summary